An aerial view of a town with a river, buildings, and surrounding greenery.

Apartments in Chestertown for Rent

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Our top choices for Chestertown apartments

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (941 reviews)
"Our room was clean, staff was friendly and a fair amount to choose from for breakfast. Would absolutely stay here again"
United States
Brandon
$103 nightly
The price is $115
Aug 23 - Aug 24
Total with taxes and fees
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (469 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
$62 nightly
The price is $68
Aug 17 - Aug 18
Total with taxes and fees
Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
8.0 out of 10, Very Good, (94 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
$111 nightly
The price is $123
Aug 2 - Aug 3
Total with taxes and fees
The Lodge at Great Oak Landing

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (178 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
$64 nightly
The price is $70
Jul 30 - Jul 31
Total with taxes and fees
Driftwood Inn

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.8 out of 10, Exceptional, (7 reviews)
"Room was very clean and the owner was very helpful will definitely stay there again"
United States
John
$141 nightly
The price is $157
Aug 10 - Aug 11
Total with taxes and fees
Haven Point Inn and Gallery

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (69 reviews)
"A beautiful place to spend a few days relaxing and enjoying nature. The owners are friendly, welcoming, and take excellent care of the property."
United States
Myrna
$200 nightly
The price is $223
Jul 30 - Jul 31
Total with taxes and fees
Inn at Huntingfield Creek

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,000 reviews)
"I have stayed several times over the last few years and the place continues to be very good."
United States
Thomas R.
$115 nightly
The price is $127
Aug 10 - Aug 11
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (943 reviews)
"Great staff and breakfast crew. Extremely reasonable price, for convenient location."
United States
Jonathan
$100 nightly
The price is $111
Aug 24 - Aug 25
Total with taxes and fees
Quality Inn Grasonville near Kent Island

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,001 reviews)
"good for a short stay"
United States
chanel
$119 nightly
The price is $133
Jul 30 - Jul 31
Total with taxes and fees
Best Western Kent Narrows Inn

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (393 reviews)
"Super clean"
United States
Joseph
$98 nightly
The price is $109
Aug 9 - Aug 10
Total with taxes and fees
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (627 reviews)
"The room was very clean and the bed was very comfortable. I enjoyed being able to have breakfast without leaving the facility and driving around to find a local restaurant."
United States
April
$89 nightly
The price is $100
Aug 27 - Aug 28
Total with taxes and fees
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,013 reviews)
"We have stayed here several times and this hotel has consistently been a wonderful stay for us!"
United States
walter
$85 nightly
The price is $96
Aug 4 - Aug 5
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,015 reviews)
"It was very clean and the staff was friendly as well as professional."
United States
LAURENCE
$89 nightly
The price is $100
Aug 4 - Aug 5
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
"Me and my husband went for a one year anniversary. Staying at the hilton was wonderful relaxing, everyone was so pleasant and helpful.The restaurants nearby were great. I love the view we'll be coming back again."
United States
Tammy
$147 nightly
The price is $163
Aug 9 - Aug 10
Total with taxes and fees
Hilton Garden Inn Kent Island Marina

Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
2.0 star property
Edgewood
6.6 out of 10, (557 reviews)
"This facility was very clean. The decor was nice. A great place to stay"
United States
Alan
$74 nightly
The price is $83
Jul 30 - Jul 31
Total with taxes and fees
Ramada Hotel & Conference Center by Wyndham Edgewood

Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very Good, (526 reviews)
"The room was very clean and had all the things you need to make a home cooked meal. Staff was very helpful with any needs and was extremely convenient to have a washer and dryer. 10/10 will definitely be staying here again."
United States
Joann
$76 nightly
The price is $85
Aug 2 - Aug 3
Total with taxes and fees
Candlewood Suites Aberdeen-Bel Air by IHG

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (168 reviews)
"Wonderful room, bar and food!"
United States
Leigh
$172 nightly
The price is $188
Aug 10 - Aug 11
Total with taxes and fees
Kent Island Resort

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,016 reviews)
"Great place to stay"
United States
Harry
$87 nightly
The price is $97
Aug 17 - Aug 18
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 star property
Edgewood
7.4 out of 10, Good, (1,187 reviews)
"Staff was fantastic and let us check in early for just a nominal fee. Thank you for a great stay!"
United States
Kyle
$65 nightly
The price is $73
Jul 30 - Jul 31
Total with taxes and fees
Quality Inn & Suites Bel Air I-95 Exit 77A

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (668 reviews)
"Friendly staff and clean room."
United States
Vivian karla
$110 nightly
The price is $123
Aug 5 - Aug 6
Total with taxes and fees
Hilton Garden Inn Aberdeen
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Top Chestertown Hotel Reviews

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
5,338
Accommodation
79 Apartments
Lowest Price
$68
Highest Price
$223

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 5 apartments in Chestertown for your vacation.
Why should you consider apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Chestertown?
First Floor Studio Apartment in Historic Chestertown: Includes a private pool, free WiFi, and private patios. A fitness center and onsite laundry facilities are on site. Historic Downtown Garden Oasis with Private Patio: Free WiFi, outdoor space, and separate dining areas are included.
How many apartments can I expect to find in Chestertown?
Expedia has 5 apartments to book in Chestertown.
What can I expect from the weather during my trip to Chestertown?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chestertown. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What should I see and do in Chestertown?
Cultural attractions include Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland, whereas Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Chestertown Historic District and Rolphs Wharf Marina.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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